Lawesson's reagent → HCID 136113976, compound

HRID 620173Notes

Reaction equation

HRID 620173 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[CH:18]=[C:17]([CH2:19][CH2:20][CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([CH2:29][CH:30]([CH3:32])[CH3:31])=[CH:25][CH:24]=3)[S:16][C:10]=2[NH:11][C:12](=O)[CH2:13][N:14]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:42])=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]2[CH:18]=[C:17]([CH2:19][CH2:20][CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([CH2:29][CH:30]([CH3:32])[CH3:31])=[CH:25][CH:24]=3)[S:16][C:10]=2[NH:11][C:12](=[S:42])[CH2:13][N:14]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 136029103HCID 136029103, compound

Product 1

HCID 136113976HCID 136113976, compoundYield 143.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 8.9 g of 5-(2-chlorophenyl)-7-[4-(4-isobutylphenyl)butyl]-1,3-dihydro-2H-thieno[2,3-e]-1,4-diazepin-2-one, melting at 133°-135° C. and 4.7 g of Lawesson reagent in 100 ml of toluene is stirred at 38°-40° C. for an hour. The resultant solution is concentrated under reduced pressure, and the residue is subjected to chromatography on silica gel and then eluted with chloroform-methanol (100:1 to 100:2). The objective fraction is concentrated under reduced pressure to give 8 g of 5-(2-chlorophenyl)-7-[4-(4-isobutylphenyl)butyl]-1,3-dihydro-2H-thieno[2,3-e]-1,4-diazepine-2-thione, melting at 169°-171° C. with decomposition.

Workup

  1. concentrationThe resultant solution is concentrated under reduced pressure
  2. washeluted with chloroform-methanol (100:1 to 100:2)
  3. concentrationThe objective fraction is concentrated under reduced pressure

Sources & evidence

ORD record
ord-c21fdb86173541808b1fde7abdfdd813
Source dataset
uspto-grants-1989_04
Patent number
US04820703

Reaction notes

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